Tetrahedron

Reductive cleavage of benzannelated cyclic ethers and amines: synthetic applications

U Azzena, S Demartis, L Pilo, E Piras

Index: Azzena, Ugo; Demartis, Salvatore; Pilo, Luciano; Piras, Elisabetta Tetrahedron, 2000 , vol. 56, # 42 p. 8375 - 8382

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Citation Number: 26

Abstract

Reduction of symmetrical intramolecular diarylmethyl ethers (3a and 8a) and amines (3b and 8b) with alkali metals in THF allows the generation of unsymmetrical oxy-or amino- functionalised arylmethyl organometallics. Such intermediates were successfully trapped with various electrophiles, allowing a new access to unsymmetrically 2, 2′-disubstituted-1, 1′-biaryls (5aa–5bf) and 1, 8-disubstituted naphthalenes (10aa–10be).